(2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester

Base Information

• Chemical Name: (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester
• CAS No.: 151073-98-2
• Molecular Formula: C₁₁H₁₅BrO₄S
• Molecular Weight: 323.208
• Mol file: 151073-98-2.mol

Synonyms:(2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester

Chemical Property of (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester

There total 4 articles about (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Benzenesulfonic acid (2S,3R)-3-ethyl-oxiranylmethyl ester → (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester (151073-98-2)

Guidance literature:

With diethylaluminium chloride; diethylamine hydrobromide; In dichloromethane; at -15 ℃; for 4h;

DOI:10.1021/ja964080b

Reference yield:

[(2S,3R)-3-ethyloxiran-2-yl]methanol (106034-58-6) → (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester (151073-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 23 °C

2: 5.98 g / HNEt₂*HBr; Et₂AlCl / CH₂Cl₂ / 4 h / -15 °C

With dmap; diethylaluminium chloride; diethylamine hydrobromide; triethylamine; In dichloromethane; 1: Esterification / 2: Ring cleavage;

DOI:10.1021/ja964080b

Reference yield:

benzenesulfonyl chloride (98-09-9) → (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester (151073-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 23 °C

2: 5.98 g / HNEt₂*HBr; Et₂AlCl / CH₂Cl₂ / 4 h / -15 °C

With dmap; diethylaluminium chloride; diethylamine hydrobromide; triethylamine; In dichloromethane; 1: Esterification / 2: Ring cleavage;

DOI:10.1021/ja964080b

upstream raw materials:

[(2S,3R)-3-ethyloxiran-2-yl]methanol

benzenesulfonyl chloride

Downstream raw materials:

(+)-isolaurepinnacin

Refernces

• 1、 Berger, Daniel,Overman, Larry E.,Renhowe, Paul A.. "Total synthesis of (+)-isolaurepinnacin. Use of acetal-alkene cyclizations to prepare highly functionalized seven-membered cyclic ethers". . p. 2446 - 2452. Retrieved 2007/10/03.